Nine Months, a Quarter of a Million Pounds, and No Hindsight

I never once made the call in under nine months. By the time I did, it had usually cost around a quarter of a million pounds.

The maths is not complicated, which is what makes it so uncomfortable. A senior hire on a £150k salary costs something like £30k in recruitment time and agency fees before they have even walked through the door. Get it wrong, and even the cleanest possible exit, three months in, no drama, everyone shakes hands, costs another £40k or so on top: notice, severance, the cost of the search starting again from zero. I never fired anyone at three months. Not once, in all my years running Happen. Not because I lacked the stomach for it. Because at three months, I genuinely could not tell whether the decision had been wrong. By the time I could tell, with something close to confidence, it had usually been nine to twelve months, and the number sitting under the decision was closer to a quarter of a million pounds than to forty thousand.

With hindsight, every single one of those calls looked like it should have been made sooner. That is precisely the trap. You never get to make the decision with hindsight. You make it walking forwards, into the fog everyone in that position has always walked into, and the fact that it looks obvious afterwards tells you nothing useful about how obvious it was at the time.

Why the textbook advice doesn't survive contact with reality

There is no shortage of writing on how to hire and fire senior people well. Watch the lead indicators, the books say. Don't wait for lagging outcomes like revenue or profit, which arrive too late to be useful. Watch meetings booked, watch command of the proposition, watch the early signals that tell you where this is heading before the number does.

It is good advice. It is also, in my experience, a great deal cleaner in a book than in a diary. In professional services sales with a long lead time, the gap between hiring someone and knowing whether they can actually do the job is not primarily a function of their skill. It is a function of luck. Whether the first three meetings land in month two or month five has as much to do with a prospect's own internal timing, a competitor's contract renewal date, a reorganisation nobody could have seen coming, as it does with anything the person you hired is doing right or wrong. You can watch the lead indicators religiously and still be watching noise for the first six months, because the underlying signal has not had time to separate from the luck sitting on top of it.

There is research that explains why this particular flavour of decision resists intuition even while intuition is exactly what most of us fall back on. Daniel Kahneman spent much of his career sceptical of gut feel; Gary Klein spent his defending it. In 2009 the two of them sat down together, properly, to work out where they actually disagreed, and where the evidence forced them to agree. Their conclusion was that trustworthy intuition only develops under two conditions: an environment regular enough to have learnable patterns, and enough repeated exposure to those patterns, with fast, clear feedback, to actually learn them. A firefighter or a chess player gets both. A founder hiring a senior salesperson gets neither. The feedback loop is nine months long if you are being rigorous about it, the outcome is heavily contaminated by luck, and most of us make this specific decision a handful of times in an entire career, nowhere near the volume of repetition needed to build real pattern-recognition.

That is a more useful way to think about it than "trust your gut," which is the advice everyone reaches for once the spreadsheets have failed them. Kahneman and Klein's own conditions rule gut feel out too: hiring a senior salesperson doesn't have the regularity or the fast feedback that trustworthy intuition needs, so confident instinct here is no more reliable than the lead indicators were. Neither the data nor the gut actually resolves the fog. That is the real finding. Not a better tool, the absence of one.

What actually slows the decision down

None of the above fully explains the nine-month number. The rational case for waiting for real signal only gets you so far. The rest is psychological, and it has a name, or several names, sunk cost among them: once you have committed the recruitment fee, the onboarding, the introductions to your biggest clients, the six months of coaching and second chances, admitting the decision was wrong means admitting that all of it was wasted, not just the salary. There is a face-saving cost too, quieter but just as real. You made this call. You defended it in the leadership meeting when someone else raised a concern in month four. Reversing it is not just an operational decision, it is walking back your own judgement in front of the people who watched you make it.

None of this is a character flaw specific to me or to founders generally. It is what happens to anyone who has to live a decision forward rather than judge it backward.

The same problem, three different currencies

What I have come to think is that this is a genuinely universal leadership problem, but it is not the same problem everywhere, because what is actually at stake changes completely depending on who is making the call.

For a bootstrapped founder, the currency is capital, and it is personal. There is no fund behind you absorbing the loss. A bad hire is not an abstract line item, it is money that came out of the business you built with nothing else behind it, which is precisely why the caution runs so deep and the decision takes as long as it does.

For a VC-backed founder, the currency is different. It is not your money in the same direct sense, so the caution that comes from personal financial exposure is largely absent. What replaces it is speed. A mis-hire in a venture-backed company does not threaten your house, it threatens your runway and your position relative to a competitor moving faster, inside a fundraising clock that does not pause for a bad decision to become undeniable.

For a public company board appointing a senior leader, or a chief executive, the clock is different again, and the honest question is rarely asked out loud: how much can any single senior appointment actually move a company of that size in the first year or two. Most of what shows up in the results during that window is inertia, decisions made and momentum built years before the new person arrived. Judging them on it anyway is common practice. It is also, on the evidence, close to judging the wrong thing entirely.

Whose evidence, and whose conclusion it was built to support

Anyone looking for research to settle this will find plenty, and almost none of it neutral. Venture capitalists cite the studies showing that replacing founders improves outcomes, because it validates a practice many of them were already inclined to do. People who believe deeply in founder-led leadership cite the studies showing founder-led public companies outperform, because it validates a story they already wanted to be true. I went looking for the strongest version of both cases recently, closely enough to see how much weight each one can genuinely bear, and the honest answer in both cases was less than either side claims. Not because the researchers were dishonest. Because the underlying decision, whether to hire, whether to fire, whether to replace, is exactly the kind of low-feedback, high-noise problem that resists clean measurement, and everyone reaching for a study to back their instinct is doing what I did for years without a study at all: making the call, then building the justification afterwards.

Where this leaves it

I do not think there is a fix for this, in the sense of a framework that removes the fog. What I think is true is that the fog is the actual condition of the job, not a failure to plan properly, and pretending otherwise, with a lead-indicator dashboard or a 90-day review process that promises clarity it cannot deliver, mostly just moves the discomfort around rather than removing it.

Hindsight will always tell you that you should have moved faster. It told me that every time. The only honest response I have found is to remember that hindsight was never available at the point the decision actually had to be made, and that the person who made it slowly, at real cost, was living forward through exactly the fog you are looking back through now.

The trap was never the nine months. It was expecting the fog to lift by month nine. It rarely does. You just have to decide inside it, on the date you agreed to, whether it's lifted or not.

Note on sourcing: Daniel Kahneman and Gary Klein, "Conditions for Intuitive Expertise: A Failure to Disagree," American Psychologist 64, no. 6 (2009): 515–526.